5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid

• ChemBase ID: 51
• Molecular Formular: C8H14O2S2
• Molecular Mass: 206.32556
• Monoisotopic Mass: 206.04352169
• SMILES: S1SCC[C@H]1CCCCC(=O)O
• Canonical SMILES: OC(=O)CCCC[C@H]1SSCC1
• InChI: InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
• InChIKey: AGBQKNBQESQNJD-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
• IUPAC Traditional name: lipoic acid
• Brand Name: Heparlipon; Biletan; Thioctsan
• Synonyms: Lipoate; Thioctic acid; alpha-Lipoic acid; 1,2-Dithiolane-3R-pentanoic acid; α-Lipoic acid (alpha lipoic acid); 6,8-Dithiooctanoic acid; DL-6,8-DITHIOOCTANOIC ACID; (R)-6,8-Dithiooctanoic acid; (R)-6,8-Thioctic acid; (R)-(+)-1,2-Dithiolane-3-pentanoic acid; (R)-(+)-1,2-Dithiolane-3-pentanoic acid; Lipoic Acid; (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid; (R)-(+)-α-Lipoic acid; (R)-6,8-二硫辛酸; (R)-6,8-硫辛酸; (R)-(+)-1,2-二硫戊环基-3-戊酸; (R)-(+)-1,2-二硫戊环基-3-戊酸; (R)-(+)-α-硫辛酸

Database IDs

• CAS Number: 1200-22-2; 1077-28-7; 62-46-4
• MDL Number: MFCD01631142
• PubChem SID: 24881001; 160963514
• PubChem CID: 6112
• CHEBI ID: 30314
• ATC CODE: A16AX01
• CHEMBL: 134342
• Chemspider ID: 5886
• DrugBank ID: DB00166
• KEGG ID: C16241
• MeSH Name: Lipoic+acid
• Wikipedia Title: Lipoic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.523468
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0948822
• LogD (pH = 7.4): -0.6761287
• Log P: 2.1137793
• Molar Refractivity: 54.3714 cm^3
• Polarizability: 21.431002 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.75
• LOG S: -2.96
• Solubility (Water): 2.24e-01 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble; Soluble as sodium salt in water; Soluble in ethanol
• Apperance: Yellow needle-like crystals
• Melting Point: 48-52 °C(lit.)
• Flash Point: >110 °C; >230 °F
• Optical Rotation: [α]/D +115±5°, c = 1% in ethanol; [α]20/D +104°, c = 1 in chloroform
• Hydrophobicity(logP): 2.1

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Bioavailability: 30% (oral)

Product Information

• Purity: ≥98.0% (HPLC); 95+%; 97%
• Grade: analytical standard
• Optical Purity: enantiomeric excess: ≥98.0% (HPLC)
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C8H14O2S2
• Classification: Genuine Natural Compounds

DETAILS

DrugBank - DB00166

• Drug Groups: approved; nutraceutical
• Description: A vitamin-like antioxidant. [PubChem]
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance.
• Pharmacology: Lipoic acid (or α-lipoic acid) is able to pass the blood-brain barrier and is putatively used for detoxification of mercury attached to the brain cells. It can mobilise bound mercury into the blood stream as it is a mercaptan (sulfur compound which readily binds to the mercury). In the blood stream, another chelator such as dimercaptosuccinic acid (DMSA) or methylsulfonylmethane (MSM) is used to transfer mercury safely into the urine for excretion. Neither DMSA nor MSM can cross the blood-brain barrier, which is why both lipoic acid and DMSA are used. It is hypothesized that this treatment-along with carnitine, dimethylglycine (DMG), Vitamin B6, folic acid, and magnesium—could be used to treat autism and amalgam poisoning. In this hypothesis, the reason why autism is difficult to treat is that mercury is attached to the brain cells and most medicines and vitamin supplements do not penetrate the blood-brain barrier. However, α-lipoic acid and perhaps vitamin B12 could making it possible for other chelators to remove mercury safely out of the body and could perhaps one day be used as a treatment for autism. Because lipoic acid is related to cellular uptake of glucose and it is both soluble in water and fat, it is being used for treatment in diabetes. It may be helpful for people with Alzheimer's disease or Parkinson's disease.
• Affected Organisms: Humans and other mammals
• References: Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. [Pubmed] ; REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - 07039

Analysis Note
identity confirmed by LC-MS
Biochem/physiol Actions
(R)-(+)-α-Lipoic acid was shown to significantly increase pyruvate oxidation while abrogating fatty acid oxidation in rat hepatocytes. These effects make R-(+)-α-Lipoic acid a promising treatment option for the treatment of Type II diabetes. 1

Sigma Aldrich - 579602

Packaging
1 g in glass bottle

MP Biomedicals - 05214667

MP Biomedicals Rare Chemical collection

REFERENCES

• Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. Pubmed
• REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. Pubmed